Calabria is definitely a unique and often weird dude, no doubt.
But one thing about him....he wants to stay in his job for 4 more years, and he will do whatever he thinks it takes for that.
To that end, I can also foresee him forging a relationship with Yellen that helps him meet his goals of staying in office and ending the conservatorship.
In fact, I believe that he will likely be in a stronger position in a post Trump presidency, as I believe he has been mostly under the thumb of Trump and Mnuchin in the current administration.